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Amine to Amide

(T3P)







Mechanism:



Carboxylic Acid to Acid Chloride


Steps:

  1. The base deprotonates the carboxylic acid.
  2. The resulting carboxylate attacks the T3P.
  3. The amine attacks the now activated carboxylic acid derived intermediate.
  4. A second equivalent of base picks up the excess proton to provide the amide.

Key Points:

  1. Base is needed for the rxn to proceed.
  2. The resulting T3P by-pdt is easily removed by aqueous work-up (usually two H2O washes is enough). The by-pdt can poison downstream rxns involving a catalyst (i.e. Pd catalyzed rxns) so care should be taken to remove most of it.



Related Books: